Just bought my first Jeep, a 1990 YJ. My first major upgrade is to do some work to the dash area, and work my way back from there. I want to replace the gauge housing with a black one, which means I will also have to paint the rest of the dash since it is a blueish-grey color. I am also looking to replace the gauges with some aftermarket gauges, the stock speakers and a new cd player.

First, how difficult are these upgrades going to be? Taking all this apart, painting the dash, etc.? I'm not exactly the most car savvy person, but would love to learn and do some of this stuff myself.

Second, how difficult is replacing the gauges and the speakers? Should I go ahead and replace the circuit board for the gauges as well?

Third, since all of this is in the same area, should I buy this stuff a little along and do all of it at one time, or a little bit along as I buy the stuff?

to replace the speakers you will need to take the dash off.
I would look at updating the dash color and speakers at the same time.

The gauges can all be removed/replaced without removing the entire dash.
The gauges in the middle are all connected by a flexible circuit board that will arc to the chassis if you are not careful removing it. This is the line for the always on Clock so you need to pull that fuse, disconnect the battery or be really really careful and pay attention the bottom of the gauge cluster doesn't touch the frame.

The Cd player can be tricky in its own right. They just barely left enough room to put a stereo in there. The back of it may or may not be jammed against the air duct.

Welcome to the wonderful world if YJ's! Tasks like these can try your patience, keep calm and just look at the things your gonna work on. Wrangler were built to be pretty easy to work on. One good tip I can give you is always tag both sides of wires or wiring harnesses. Also get some plastic cups and drop you bolts in the cups and label the cups. Organization is key! Good luck, have fun and learn as you wrench!

I would personally think twice about painting the actual dash. For some reason it just never comes out right and it will always chip eventually. But that's just me. Gauges can get very expensive. But it depends i guess on what your plans for this Jeep are...And speakers...I always wonder what in the world they were thinking when they made that whole mount part on piece and made no way to get to the speakers. There's studs back there and just wedged mine in and they don't move. But all speakers are gonna be different. If you have the means though, take a wizard or a sawzall and cut those parts off of the rest so that can be unscrewed to get to later. Probably save you alot of frusteration, trust me. Magnetic trays are a deffinate. Life savers. You'll figure it out. Good luck!

Yeah, the plastic part that fits around the gauges will be replaced but my dash is an off color blue and all I can find is black or spice. That means the top part of the dash will still be that blueish color, so I'm going to have to try and paint it to match unless I can replace it too. I just can't find anywhere that sells that top part.